Studies are proposed to continue efforts in which aromatic oxazolines (phenyl, naphthyl) are utilized to introduce, in a stereospecific manner, two or more chiral centers by addition to the aromatic ring. With the appropriate choice of nucleophiles and trapping electrophiles, we hope to reach a variety of important naturally occurring, biologically active systems. This study will provide access to (+)-aklavinone, (-)-podophyllotoxin, and (+)-steganone, and key intermediates for the synthesis of chlorothricolide and lasalocid A. Extensions to additional systems to evaluate the scope of these stereochemical processes are also envisioned. Furthermore, heterocyclic aromatics containing chiral oxazolines will be studied to introduce substituents, enantioselectively, into the pyridine ring. The products of these reactions will serve as models for NADH mimics and also as highly selective chiral reducing agents. We will study those self-immolative processes to enhance the further understanding of the effects of various parameters which are responsible for high asymmetric reduction of various prochiral substrates.